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How to get fromChicago to Westchester Countyby plane, train, bus (Flixbus), train (Amtrak), car, shuttle, or bus

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There are 10 ways to get from Chicago to Westchester County by plane, train, bus (Flixbus), train (Amtrak), car, shuttle, or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Chappaquatrain train
    5h 28m
    $196–580

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Chappaquatrain train
    6h 21m
    $112–519

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    20h 29m
    $202–278

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    20h 49m
    $309–615

  5. Drive 813.2 mi

    1. Drive from Chicago to Westchester Countycar car 813.2 mi
    13h 44m
    $149–215

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Chappaquatrain train
    5h 48m
    $226–680

  7. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Chappaquatrain train
    6h 1m
    $338–891

  8. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, shuttle, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take a shuttle bus from Newark Airport Terminal B to Grand Centralshuttle bus
    3. Take the train from Grand Central Terminal to Chappaquatrain train
    6h 36m
    $218–923

  9. Fly Chicago Midway International Airport to Philadelphia International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Grand Central Terminal to Chappaquatrain train
    7h 23m
    $180–1,029

  10. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Chappaquatrain train
    23h 15m
    $180–384

Chicago to Westchester County by bus

Calendar7Weekly Buses
Duration20h 29mAverage Duration
Ticket$202Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Westchester County.ExpandLaunch map view
  • Distance: 769 mi
  • Duration: 5h 28m

What companies run services between Chicago, IL, USA and Westchester County, NY, USA?

Flixbus USA operates a bus from Chicago Bus Station to New York Midtown twice daily. Tickets cost $140–240 and the journey takes 17h 5m. Jefferson Lines also services this route once daily. Alternatively, Amtrak operates a train from Chicago Union Station to Croton-Harmon Amtrak Station once daily. Tickets cost $300–650 and the journey takes 19h 23m.

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